反应详情
EQUATION
反应方程式
REACTANTS
反应物
PRODUCTS
生成物
AUXILIARIES
试剂、催化剂与溶剂
CONDITIONS
反应条件
- 温度
- 100 °C
PROCEDURE
实验过程
A 50 mL round bottom flask charged with tert-butyl 4-(3-iodo-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (500 mg, 0.8 mmol), tri(o-tolyl)phosphine (18.25 mg, 0.06 mmol), Pd2dba3 (18.3 mg, 0.02 mmol), triethylamine (334 μL, 2.4 mmol), and DMF (7 mL) was purged under N2 (3 cycles). Next, methyl acrylate (216 μL, 2.4 mmol) was added, and the mixture was stirred at 100° C. under N2 atmosphere for 18 hours. The reaction mixture was cooled to room temperature, diluted with EtOAc (50 mL) and water (100 mL) was added. The phases were separated, and the organic layer was washed with water (3×30 mL), dried (MgSO4), filtered, and concentrated in vacuo. The residue obtained was crystallized from CH3CN to provide (E)-tert-butyl 4-(3-(3-methoxy-3-oxoprop-1-enyl)-1-(4-methoxybenzyl)-5-phenyl-1H-pyrazolo[3,4-b]pyridin-4-yl)piperazine-1-carboxylate (390 mg, 84% yield) as a solid. LCMS (APCI+) m/z 584.2 (M+H)+, Retention time=4.96 minutes.
WORKUP
后处理
- customwas purged under N2 (3 cycles)
- temperatureThe reaction mixture was cooled to room temperature
- additionwas added
- customThe phases were separated
- washthe organic layer was washed with water (3×30 mL)
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationconcentrated in vacuo
- customThe residue obtained
- customwas crystallized from CH3CN